


Five Times Dean Remembers Sex...and One Time He Doesn't

by sowell



Category: Supernatural
Genre: F/M, M/M
Language: English
Status: Completed
Published: 2013-05-27
Updated: 2013-05-27
Packaged: 2017-12-13 02:31:38
Rating: Explicit
Warnings: Rape/Non-Con, Underage
Chapters: 1
Words: 4,142
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/818926
Author URL: https://archiveofourown.org/users/sowell/pseuds/sowell
Summary: <blockquote class="userstuff">
              <p>Dean's life in sexual encounters.</p>
            </blockquote>





	Five Times Dean Remembers Sex...and One Time He Doesn't

_Cammie_

  
Caitlin Morey is the queen bee of Fairmont High School’s ninth grade biology class. Dean can spot it a mile away; he has an eye for these things. He snagged a seat next to her on the first day of the new term, and she’s been sliding glances at him from under her lashes for a week now. She’s not as hot as the hottest chick at Dean’s last high school, but her legs are at least as long as Dean’s and twice as gorgeous, so she’s definitely worth the effort.  
  
She lets him feel her up before he has to pick up Sam, and her skin under her bra cups makes him so hard he can barely walk.  
  
She’s smart, and Dean kinda digs that, even if he’ll never admit it. Still, when she says “study” he hears “third base,” and sure enough it takes about ten minutes before they’re flat on her bed, locked at the lips.  
  
“Yeah?” he asks, fingers hooked into the top of her jeans. God, he loves girls, with their long hair and their crazy mood swings and the way they smile at him when he makes a joke. He loves Caitlin Morey most of all, because she bites her lip and nods, and then Dean’s kissing her stomach while he unzips her jeans.  
  
“You little slut,” says a voice from the doorway, and when Dean looks up there’s another girl standing there: older, darker, and infinitely hotter than even Caitlin, which he didn’t realize was possible at the moment.  
  
The voice is mocking, not angry, and Caitlin hurls a frilly little pillow at its owner.  
  
“God Cammie, don’t you fucking knock?”  
  
Cammie Morey. Dean recognizes her now, because if Caitlin is the queen bee of the ninth grade, then Cammie is her senior year counterpart. Sisters, jesus. His head swims.  
  
“Phone,” Cammie says sweetly. “It’s dad.”  
  
Caitlin flounces off, and Cammie leans in the door, staring at him.  
  
“Hi,” Dean says. His shirt is off and he has a boner that she can probably see from across the room, but hey. He’s been in worse situations. Way worse.  
  
“Freshman?” Cammie asks, all deep dimples and assessing eyes.  
  
“Uh..yeah. Freshman.”  
  
“You look older,” she notes. “Really grown up.”  
  
Dean’s pretty sure that’s a lie, but he’ll take it. She is really smokin’ hot.  
  
“I work out,” he says, and it’s cheesy and stupid, but she laughs anyway.  
  
“At least little sis has good taste,” she says, and Dean actually blushes. He’s aware that he’s hot stuff, but this direct-compliment stuff is…weird. He does the flirting, not the other way around.  
  
“So…”  
  
“Dean.”  
  
“So Dean. You’re not still a virgin, are you?”  
  
She trails a hand down his stomach, then slides her fingers into his jeans, like it’s no big deal. Like every girl he knows just goes around, grabbing his dick.  
  
“Jesus fuck,” he says, and she laughs.  
  
She fucks him more than the other way around, and she sucks on his lips like they’re made of candy. He doesn’t even get his jeans all the way off, and she just shoves his hands under her bra instead of disrobing. He feels a little guilty, except that he came in expecting third base and Cammie just opened up and offered him a home run, and what red-blooded fourteen-year-old boy is supposed to turn that down? Plus, he has the best story to tell Sam, ever.  
  
He doesn’t completely embarrass himself. He thinks. She seems to know when he’s about to explode, and she lifts off him and lets him come on his own stomach, staring at the dark little thatch of hair between her legs. He’s pretty sure he’s in love.  
  
Caitlin  _screeches_  when she sees them, and Dean falls off the bed. She goes for her sister’s hair, and Dean scrambles out of the way, grabbing up his clothes. They’re screaming at each other and scratching, and Dean has never been so happy to have a little brother and not a crazy-ass sister.  
  
He asks to switch seats the next day in biology, but the teacher tells him they’re stuck until next term.  
  
Thank god they move around a lot.

  
_Lisa_   


  
The thing about yoga instructors is that they’re so damn…bendy.  
  
“How about this?” Lisa asks, and she folds her naked body into another pose that makes Dean groan.  
  
He tries to replicate, and fails miserably. She’s laughing at him, mouth wide and soft and hair as thick as velvet. She releases the pose with an easy shake, and Dean follows the tanned lines of her body. He swipes at her, and she twists away.  
  
“I told you,” she chides, smiling very close to his face. “Three poses, and then you get some. How hard can that be?”  
  
Dean kisses her, hands buried in all those layers of hair, and she lets him for a second before she pulls away again.  
  
“Okay,” she says. “Downward dog. Even my beginners can do this one.”  
  
He’s not used to working quite so hard for it, but Lisa Braeden is worth it. Besides, he’s not in any rush. For once, Dad and Sam seem to have struck some sort of wary truce, so Dean is free to indulge a little. And Lisa is the best indulgence he can possibly imagine.  
  
He tries the pose, but keeps getting distracted by the stretch of Lisa’s thigh and the way her tits seem to defy gravity.  
  
“Useless,” Lisa says. But she sounds breathless and happy and Dean feels warm in a way that reminds him of Kansas and baking pie and a bright yellow kitchen.  
  
“I’ll help you,” she says, and then she’s placing both of his hands on the floor, naked flesh pressed all up against him.  
  
“Okay,” she whispers. “Stomach in,” five fingers against his clenching abs, “legs planted,” two hands between his thighs, nudging them slightly apart, “neck relaxed.” She lets her fingers trail from his neck through his hair, and then Dean can’t take it anymore. He rolls, bringing both of them to the ground in a move that has her shrieking.  
  
She doesn’t stop kissing him this time, just plants two hands on his shoulders and nips at his mouth, stinging and wonderful.  
  
“How’d I do?” Dean asks later, sleepy and sated.  
  
“Not my most promising student,” she says wryly. “But we have,” her eyes flick up at the clock, “twelve more hours to improve your technique.”  
  
Dean smiles, close-mouthed, and spreads his arms under her. “Sweetheart, I’m all yours.”

  
_Sam_   


  
It’s Tuesday, and Sam is freaking out, which: what else is new?  
  
“You don’t understand.” Sam is pushing hands through his stupid hair, all hunched over on the bed. “It’s been weeks, maybe months, and I can’t…”  
  
“Slow down,” Dean says in his most placating voice. “Let’s just get breakfast and figure this out.”  
  
“No!” Sam says wildly, and he’s grabbing at Dean. “That’s always how it starts.”  
  
Dean stares at him. Sam’s eyes are churning like crazy, and he’s scared.  
  
“Okay,” Dean says, a little quieter. “Okay, I believe you.”  
  
Sam’s face just  _crumples_. “You do?”  
  
“Yeah. Sure. I mean, I’m pretty sure you’re off your frickin’ rocker, but…”  
  
“Dean!” Sam shoves him away, and Dean laughs.  
  
“Come on, I’m kidding. You obviously believe it, so let’s…”  
  
“No breakfast,” Sam says, shaking his head. “No research, no sight-seeing, no weapons-cleaning – it’s all cursed, Dean! No matter what, you die.”  
  
Dean doesn’t feel like he’s going to die. He feels hungry, and a little bewildered, but otherwise fine. Sam is a few seconds away from falling apart, though, so he sighs and sits.  
  
“Okay,” he says, hands up in surrender. “No breakfast. We won’t even leave the room.”  
  
Sam swallows, then nods. “Okay,” he says. He sits down on the other bed, and they stare at each other. And stare.  
  
“Really?” Dean asks. “All day?”  
  
Sam throws up his hands. “I don’t know what else to do!”  
  
Dean moves to stand up, and Sam pushes him back down with two hands on his shoulders.  
  
“Dude,” Dean says. “This is ridiculous.”  
  
He tries again, and Sam presses him back, hands shaking.  
  
“Quit it,” Dean says, grabbing at him.  
  
Sam’s not even hearing him. “You have…to stay…here,” he says breathlessly, catching Dean’s wrists wherever they strike out.  
  
“What is wrong with you?” Dean yells, and Sam finally just tackles him, throwing them both to the bed.  
  
Dean realizes his hands are pinned by his head and Sam has a knee pressing both of his thighs down, and there’s no way out of it without doing some serious damage to both of them.  
  
“Do you even see what’s happening, here?” Dean asks up at him. “This is insane.”  
  
Sam’s face is very close, and when his eyes screw shut, Dean can see the tension in his face, strained and pale.  
  
“You’ll thank me later,” Sam says stubbornly.  
  
Dean bucks, and Sam just drops down on him, knees sliding between his legs to push his thighs even farther apart.  
  
“You can be mad,” Sam says, “but this is the only way.”  
  
“Mad doesn’t even begin to cover it,” Dean assures him, but it’s actually kind of nice. Sam is crazy broad, firm and warm all along Dean’s torso, and the last time they were so close Sam was dying in his arms.  
  
He’s alive now, heart thudding steadily, giant hands sweaty around Dean’s wrists. He presses his forehead into the comforter, right next to Dean’s head, and Dean sees him rubbing in a hopeless, desperate sort of motion. He’s like a really solid blanket, and Dean starts to sweat.  
  
“You’re a little old for cuddles,” Dean tries.  
  
“No.”  
  
“You’re gonna have to pee eventually.”  
  
“No.”  
  
Dean turns his head, and Sam’s neck is right  _there_. He reaches out and flicks his tongue against the sun-darkened skin.  
  
Sam jerks his head up. “What the hell?”  
  
“Hey,” Dean says innocently. “You can’t pin a grown man to a bed and not expect to be molested.”  
  
Sam is glaring at him. “Don’t do that.”  
  
Dean sticks his tongue out again, this time toward Sam’s nose. Sam stretches his head back without letting up an inch on Dean’s limbs.  
  
“Cut it out,” Sam says.  
  
“Aw, Sammy,” Dean says. “I had no idea you were so shy. Just let me up and – ”  
  
“I’m warning you,” Sam says.  
  
Dean grins, and then he feels it. Sam’s cock twitches against his hip. The smile freezes on his face.  
  
“Sammy?” he says, very carefully. Neutral. Sam’s eyes are looking somewhere at the wall, and his cheeks are flushed a dull red.  
  
“What the hell?” he asks, and Sam groans, dropping his head forward. His hair tickles Dean’s face.  
  
“Just…don’t,” Sam says miserably. “Just don’t say anything.”  
  
“How can I not say anything?” Dean says, panic beginning to flutter in his stomach. “My mountain of a brother is totally losing it, I’m being held prisoner in my own hotel room, and…oh, yeah. You have a freaking ginormous hard-on.”  
  
It's  _really_  ginormous, Dean realizes uncomfortably.  
  
Sam’s face is even redder. “Look, you started it,” he says.  
  
“What?”  
  
“You licked me!”  
  
“Yeah, so you would get off of me, you freak!”  
  
“I can’t.” Sam’s tone is agonized. “I’m sorry, but I can’t. You don’t know how many times I’ve watched you die already. We’re staying like this, even if…”  
  
Even if it means Sam’s dick poking into him all day, Dean thinks. Well, screw that.  
  
He starts to struggle in earnest, but Sam bears down hard, manhandling Dean until they’re skewed halfway off the mattress, pinned at a horribly awkward angle. Jesus, Sam is a big fucker.  
  
“This is ridiculous,” Dean says. “Sam, this is – ”  
  
“Shut up,” Sam says, shuddering against him. “Just shut up.” He’s even harder, and damn it, Dean’s not exactly a model of self-control. His pulse is pounding, because Sam smells like sleep and cotton the Impala’s leather seats, and there’s only so much friction he can take.  
  
“Sam,” Dean tries coaxingly. “Come on. Let me up and we can – ”  
  
Sam kisses him, open-mouth and everything, tongue prodding at him with a desperation Dean can’t help respond to. Dean would think one of them just died, except he knows perfectly well that it’s been months, and even then it was Sam on that mattress, Sam whose heart had stopped.  
  
“Jesus,” Dean says shakily, when Sam finally pulls away. Sam is pawing at him, hands kneading in scattered, unconscious bursts, and Dean doesn’t think he could have put a stop to it even if his arms weren’t pinned.  
  
“What the hell?” he says, reedy. Sam’s mouth is on his jaw, dragging kisses.  
  
“I don’t know, I don’t know,” Sam is saying. “Just. Just let me…”  
  
Sam moves them both back on the bed, and Dean lets himself be shoved, even though Sam has let him up and he could, conceivably, escape this completely bizarre hotel room scene. Instead, he looks up as Sam crawls over him, all muscled arms and worried eyes and red, messy lips.  
  
“I’m sorry,” he says, but he’s looking at Dean’s mouth, eyeing it like he’s deciding how to attack it next.  
  
“I can tell,” Dean says. He lifts a thigh and rubs it against Sam’s crotch, feeling how hard he is.  
  
“I didn’t mean for this to – ”  
  
Dean yanks him down by a fistful of shirt, and Sam lets him. Their chests slam together, and Dean realizes he’s gone from freaked out to turned-on in minutes flat, mainly because Sam’s mouth tastes like mint and sugar and all things awesome.  
  
Sam is making whimpering little noises that Dean should mock him for, but they’ve both boarded this one-way train to hell together, so he doesn’t think he has much room to judge. He can’t get Sam’s shirt off fast enough, pulling and stretching in frustration. Sam’s hands are down his boxers, stroking him in this rough, fast rhythm that has Dean’s eyes rolling back in his head.  
  
Sam flips him like a pancake, and Dean gets a mouth full of scratchy bedcovers and cotton pillowcase.  
  
“Keeping you alive,” Sam is saying behind him. “Won’t let you, not today.”  
  
Dean doesn’t really have time to decipher any more crazy talk at the moment, and so he hitches his hips up, reaching down to pull at his own dick.  
  
“Come on,” he says over his shoulder. “You better finish this, or you and I are having it out later.”  
  
Sam gives a choked laugh, and then one long finger is sliding into Dean, prodding. Dean moans in a way that even sounds pornographic to his own ears, and he rocks back. It feels so weirdly wrong, all stretched and full, and Dean thinks he wants about ten more of Sam’s fingers in there, slim and strong and possessive.  
  
His heart is beating so fast that he can hear it in his ears, behind his eyes. He’s panting uncontrollably into the mattress, and it’s making him a little light-headed. He’s never let himself think about this, never let Sam catch a hint of this particular dysfunction. But now it’s happening, thanks to whatever bizarre phobia is plaguing Sam, and Dean can barely breathe with the shocked pleasure of it.  
  
Sam is a fucking genius, he’s a monster, he’s the thing that Dean can’t look at too long without hurting his eyes. He’s going to combust right here on this bed before he comes, because Sam’s chest is slick and broad against his back, and his fingers are thrusting in the roughest, dirtiest rhythm Dean can imagine.  
  
He gasps for breath. It’s too much. He can’t get in enough air, and somehow everything but the feel of Sam’s fingers is fading around him.  
  
“Dean?” He hears Sam’s voice, tinny and far away, and then a pain slices through his chest, making him double up.  
  
“Oh god, Dean,” Sam is saying, but Dean can’t hear him. His chest is on fire, heart jerking when it should be pounding, oxygen nowhere to be found. He’s suffocating, and he realizes he’s just let his baby brother fuck him to death.  
  
Sam’s hands are on him, and then everything fades out, and…  
  
It’s Tuesday, and Sam is freaking out, but what else is new?

  
_Alastair_   


  
They got some things wrong about hell, Dean thinks. The fire and brimstone, sure. But everything burns cold, not hot. He shivers, even as red washes over his vision.  
  
He’s face down on the floor, not on the rack, but it doesn’t matter anyway. It’s always Alastair and him, forever and ever, on loop.  
  
Alastair steps on his back, pressing. A rib cracks, and Dean struggles to breathe.  
  
“It could stop,” Alistair whispers, sinuous and pleasant. “You know how you can make it stop.”  
  
“Your stand-up act needs some work,” Dean manages. “Getting old.”  
  
Sometimes Alastair is Sam and sometimes he’s Dad and sometimes he’s Mom, even, smiling coldly in her sweet face. Today he’s just himself, twisted coal face and cruel, taloned hands.  
  
It hurts more when Alistair uses his fingers, but it’s more humiliating when he uses the butt of the whip, and that’s what he does today. It’s rough, and thick, and it makes Dean bleed, but it’s not the worst they’ve attacked him with.  
  
 _Sam_ , he tells himself.  _Sam is alive. Everything else is worth it._  It’s kept him going for almost twenty years, but it’s getting harder to remember, nowadays.  
  
Alastair flips him over when he’s done, one booted foot under Dean’s chin, shoving. Dean hisses as his torso twists, aggravating his broken rib.  
  
“Dean, Dean, Dean,” Alastair says, shaking his head sadly. “You can’t take much more of this. Eventually, you’ll make the right choice.”  
  
“Fuck you,” Dean says, then coughs as Alastair pops another rib.  
  
“Little late for that,” the demon smirks, pulling out a long silver knife. “Now, what shall we do next?”  
  


  
_Castiel_   


  
Castiel watches Dean in Purgatory. Dean supposes Castiel has always watched him, but in this hellhole his options for dealing are limited to 1) stare back, or 2) ignore. Dean’s been ignoring uncomfortable shit long before Purgatory bit him in the ass, so Castiel is pretty easy.  
  
Except that he tends to talk, and all too often it’s less the “this is how we should survive” kind of talk and more the “peel Dean’s soul back one layer at a time” kind of talk, and that’s about the last thing Dean needs.  
  
So sometimes, when Castiel says useless things like, “You think Sam should have been here by now,” or “You look pensive,” or “This head wound may cause you permanent brain damage,” Dean just puts a hand over his face and physically turns him away. It’s usually accompanied by some sort of order that Castiel either follows obediently or ignores entirely, depending on his tenuous angel mood swings.  
  
One time, though, Castiel just catches his wrist and holds it there, enormous strength in his fragile body, tilted head and probing eyes.  
  
“I don’t mind being a substitute for Sam,” he says. “Angels aren’t bothered by things like that.”  
  
And that’s how Dean ends up on top of him, more than a little angry, furious and heartsick and realizing that, no matter how brutally he drives into him, Castiel’s pulse isn’t even going to pick up.  
  
Dean’s not that good at brutal, anyway. With a gun, sure. But with sex? He’ll never admit it out loud, but he’s more puppy than lion in the sack. It’s just that a good orgasm has always turned him to mush, and he can’t help his happy glow when one is imminent. Besides, he’s never had any complaints.  
  
But Castiel clearly doesn’t understand how to take the initiative, so Dean’s left like this, having sex in a way that isn’t anything like satisfying, with someone whose face both calms his demons and creeps him out in equal measure.  
  
At least Cas is hot. He’s not Sam-hot and not anywhere near Lisa-hot, but his skin glows pale under Dean’s mouth, and his lips taste like the only clean thing in Dean’s life.  
  
“That didn’t help,” Cas tells him afterward, when Dean is hiking his jeans back up and resisting the urge to punch the nearest tree into smithereens. “Maybe we should try another position.”  
  
Dean’s laugh is half-choked. “No,” he says. “I think we can count that out as entertainment.”  
  
Castiel never brings it up again.

  
_Sam_   


  
“Dean!” Sam is shaking him, and it fucking hurts.  
  
“Oooow,” Dean moans, hand going to his eyes. His head is pounding.  
  
And he’s dripping wet.  
  
“I’m wet,” he says hoarsely. “Why am I wet?”  
  
“Because a mermaid tried to drown you,” Sam all but yells, and Dean shuts his eyes.  
  
“Dude, volume,” he says.  
  
Dean remembers. Mermaid chick. Sea shell bra. Not so cute when she was doing her whole flesh-eating decaying-skin routine.  
  
“Did I get her?” Dean asks.  
  
“ _I_  got her,” Sam huffs, and Dean supposes that’s good enough.  
  
Sam pulls him to his feet and he just sags, water sloshing all around where his brain should be. “I hate the ocean,” Dean mumbles.  
  
Sam props him up, slapping him on the back none-too-gently. Dean spits out a little more water, then groans as his head attacks him again.  
  
“Hey, you okay?” Sam asks warily.  
  
“Fine, just…ocean.”  
  
“Well next time don’t chase some girl out on her houseboat just because she has a sea shell bra.”  
  
Dean knows that Sam knows that he hasn’t even remotely learned his lesson, but he says, “Yeah. Gotcha.”  
  
“I mean it,” Sam says impatiently. “Just…keep your goddamn dick in your pants for once. You’re thirty years old, not a teenager.”  
  
Dean’s too tired and achy to start a full-scale war, but he’s pissed enough to smile with all his teeth and say, “A man has his needs, Sammy.”  
  
“It’s not need, it’s compulsion,” Sam mutters.  
  
“Hey, just because you’re doomed to celibacy, doesn’t mean the rest of us have to suffer.”  
  
Sam pushes him into the nearest wall, and Dean’s shoulder bounces off the brick. “This isn’t funny. You almost died, Dean.”  
  
Dean glares at him. “We almost die every day. At least I would have died happy.”  
  
Sam’s reached the hair-pulling stage, so Dean sighs and takes pity.  
  
“Look,” he says, backing away. “I’ll be more careful, all right? No more late night hookups without checking in with my nanny.”  
  
“Whatever,” Sam says, and starts to walk away. Then he stops, and turns back. “You know what?” he says, getting right in Dean’s face. “Not whatever. Because I’m sick and tired of watching this happen to you. There’s a lot of shit we don’t have control over, but this? These stupid decisions? That’s all on you.”  
  
Dean blows out a hard breath. “Then what, huh? Because this is me, Sammy. You’ve known me your whole life. Don’t expect miracles now.”  
  
And Sam shoves Dean flat against the wall, crowding him with the width of his body. “This is what,” Sam says, and hikes his tongue down Dean’s throat. Dean’s heart slams, more from the shock than from anything else, and he presses his hands backwards, flat against the brick.  
  
Sam breaks away, flushed and satisfied, eyes gleaming. “You want to go chase after some chick, find me instead. Trust  _me_. There are a million things out there trying to get us, but I’m not one of them. If you need to, use  _me_.”  
  
It takes Dean a moment to find his voice. “That’s…that’s disgusting,” he says.  
  
“You have a boner right now.”  
  
Fuck Sam and his observational skills.  
  
“Yeah, well, I was a few seconds from closing the deal when that mermaid went all Night of the Living Dead on me,” Dean babbles. “She left me high and dry, man. I mean, you can’t expect me to just turn it off and on.”  
  
Sam kisses him again, just his stops his mouth with hard lips and a freakishly long tongue, and Dean lets him. Really, what’s the harm? It’s probably just a phase, and once Sam’s anger cools down he’ll realize how completely out-of-whack this whole suggestion is, and Dean can pretend like this never happened. Like Sam never licked the salt from his lips and pressed their hips together, and made Dean feel like he might explode. Like he’s fourteen again and Caitlin or Cammie or what’s-her-name just sat on his dick for the first time and blew his mind.  
  
“This is seriously screwed up,” Dean says when Sam finally pulls away.  
  
“What else is new?” Sam shrugs. “If you can wait ten freaking minutes I got us a double bed.”  
  
Dean considers. “Okay,” he says. “But I reserve the right to call a do-over in the morning.”  
  
“Whatever,” Sam says.  
  
“Bitch.”  
  
“Jerk. Are you coming?”  
  
Yeah, Dean suspects he is.


End file.
